Craftsman’s team is unique for a technology company of our size. Approximately three quarters of our staff live in the Greater Boston area, co-locating in our office near South Station. The remaining quarter live and work from their homes in other states. Given our hybrid staffing model, staff retreats are an essential component to our success. They provide an opportunity to take stock of where we’ve come from and where we want to go, collaborate with colleagues we may not work with on a daily basis, and help the team build social connections.
COVID-19 changed the way organizations do business. Team building and professional development were not immune to these changes. After initially delaying and then cancelling our in-person Spring retreat, we pivoted to a remote format. To turn the remote retreat from an idea into reality, a four-person planning committee began meeting weekly. The team made careful decisions, keeping in mind the variety of challenges – and advantages – that come with remote work. In this post, we highlight lessons learned from planning and executing Craftsman’s first-ever remote retreat.
Organization + Logistics
As a professional services firm, our time is our product and our client work never stands still. Our staff would need time to attend to their client work during the week. And, as perpetual Zoom-ers we knew it would be exhausting to be on video all day, every day. We quickly realized that a remote retreat is not an in-person retreat that happens to take place over Zoom. While back-to-back sessions and events might make sense in person, a more realistic expectation for a remote retreat would be afternoons only. This left the mornings open for managing client work, and afternoons for coming together to discuss, learn, and socialize. As a result, staff members felt focused, energized, and were not distracted with multitasking.
In addition to timing and logistics, a theme was also an essential element to keeping focus during the multi-day retreat. The planning committee and management team needed a clear purpose. We considered the questions: “Why are we gathering?” And, “Why now?” For Craftsman, this was celebrating our upcoming fifth birthday and continued growth. The firm is experiencing some classic growing pains for a company of our size and we wanted to focus particularly on how we communicate and collaborate with one another. This was a timely, important topic and felt like a natural focus for our conversations.
Narrowing session topics meant strictly maintaining theme focus. We started with a long list of proposed sessions. As we reviewed each one, we discussed whether that topic needed to take place specifically at this retreat, or if it could be covered in a standalone staff meeting. We slowly trimmed down our list, eliminating or delaying sessions for non-retreat time, until we reached a realistic schedule. Our schedule also included plenty of social time, which is generally a highlight of staff retreats.
The Fun Stuff
People like swag, even at home. The planning team put together branded gear and snacks to keep the team energized. We boxed them up and shipped them to arrive sometime during retreat week. The package was relatively inexpensive and easy to organize, it just took a bit of advanced planning. And, the gesture seemed to go a long way.
Social time was still a priority. While we grieved not being together for dinners, happy hours, and casual side conversations, we knew this would be an important component of our remote retreat. Each day included some element of fun, such as live games with the entire team or in smaller breakout groups. One of the days included a “speed dating” style rotation, where each person spent 20 minutes talking to a colleague they do not work with regularly. We also sprinkled some “show-and-tell” sessions throughout the retreat, where one participant spent three minutes showing us something from their home and sharing the story behind it. For the final day, we brought in Kingmakers, a gaming company that facilitates games for remote teams like ours.
Feedback + Communication
Open communication and feedback should take place before, during, and after the retreat. Knowing that group discussions can feel a bit stilted for many, we sent out a survey the week before to get our team’s thoughts on Craftsman’s communication practices and collaboration tools. This provided some useful data to base discussions on and made participation easier. It also gave us a clearer idea of where we were doing well and where we needed some improvement. A simple Google Form provided us with helpful graphs and quotes to frame our discussions. We also leveraged Google Calendar for our retreat agenda, which we shared with staff the week before. The calendar allowed us to updated Zoom links and agendas on the fly, without having to direct people to the right place in between sessions.
Post-retreat, we used available tools to keep the conversation going. Our retreat Slack channel was a lively place throughout the retreat and long after. We used the channel for “parking lot” items, follow ups, and presentation decks. This channel also supports our efforts to follow through on the rich discussions that took place during retreat week.
Summary + Conclusion
As we closed out the retreat, the reviews were overwhelmingly positive. The timing helped participants stay focused and energized. We had a good mix of topics and a balance between learning and social sessions. And, our focus felt timely for where our firm is in its growth. One participant pointed out that even when we return to in-person retreats, this week gave us some wonderful ideas on how to better engage with each other remotely throughout the year. While planning a remote retreat was not originally part of this year’s plan, the shift turned out to be a challenging exercise resulting in a meaningful, collaborative, and energizing retreat for our staff.